DE2116079C3 - 6,7-Dimethoxy-chinazoline - Google Patents
6,7-Dimethoxy-chinazolineInfo
- Publication number
- DE2116079C3 DE2116079C3 DE19712116079 DE2116079A DE2116079C3 DE 2116079 C3 DE2116079 C3 DE 2116079C3 DE 19712116079 DE19712116079 DE 19712116079 DE 2116079 A DE2116079 A DE 2116079A DE 2116079 C3 DE2116079 C3 DE 2116079C3
- Authority
- DE
- Germany
- Prior art keywords
- compound
- dimethoxy
- methyl
- mmol
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FYMQPWWNOCENRN-UHFFFAOYSA-N 6,7-dimethoxyquinazoline Chemical class N1=CN=C2C=C(OC)C(OC)=CC2=C1 FYMQPWWNOCENRN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- GVYLPHXTENDOCD-UHFFFAOYSA-N ethyl 1,2-dihydroquinazoline-2-carboxylate Chemical compound C1=CC=C2C=NC(C(=O)OCC)NC2=C1 GVYLPHXTENDOCD-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- ROSBRNVZLBSBHG-UHFFFAOYSA-N 6,7-dimethoxy-2,3-dimethyl-1,2-dihydroquinazolin-4-one Chemical compound COC=1C=C2C(N(C(NC2=CC1OC)C)C)=O ROSBRNVZLBSBHG-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003204 tranquilizing agent Substances 0.000 description 7
- 230000002936 tranquilizing effect Effects 0.000 description 7
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl radical Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229940125725 tranquilizer Drugs 0.000 description 6
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000001629 suppression Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 230000037023 motor activity Effects 0.000 description 4
- GKJZZPGNBQWSAV-UHFFFAOYSA-N 6,7-dimethoxy-2,3-dimethylquinazolin-4-one Chemical compound N1=C(C)N(C)C(=O)C2=C1C=C(OC)C(OC)=C2 GKJZZPGNBQWSAV-UHFFFAOYSA-N 0.000 description 3
- 206010003591 Ataxia Diseases 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 231100001160 nonlethal Toxicity 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 206010054089 Depressive symptom Diseases 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- PAALZYWYTHQUFI-UHFFFAOYSA-N 1,2-dihydroquinazoline-2-carboxylic acid Chemical compound C1=CC=C2C=NC(C(=O)O)NC2=C1 PAALZYWYTHQUFI-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-3H-quinazolin-4-one Natural products C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 1
- OXKGPRFZOMWISI-UHFFFAOYSA-N 3-ethyl-6,7-dimethoxy-2-methyl-4-oxo-2H-quinazoline-1-carboxylic acid Chemical compound COC=1C=C2C(N(C(N(C2=CC1OC)C(=O)O)C)CC)=O OXKGPRFZOMWISI-UHFFFAOYSA-N 0.000 description 1
- IMMXADOJWVVPQB-UHFFFAOYSA-N 3-ethyl-6,7-dimethoxy-2-methylquinazolin-4-one Chemical compound COC=1C=C2C(N(C(=NC2=CC1OC)C)CC)=O IMMXADOJWVVPQB-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- OJZARWXFPRLPGP-UHFFFAOYSA-N 6,7-dimethoxy-3-methylquinazolin-4-one Chemical compound N1=CN(C)C(=O)C2=C1C=C(OC)C(OC)=C2 OJZARWXFPRLPGP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MAZMPXLFEOXKPB-UHFFFAOYSA-N CCN(C(C)N(C(OCC)=O)C(C1=C2)=CC(OC)=C2OC)C1=O Chemical compound CCN(C(C)N(C(OCC)=O)C(C1=C2)=CC(OC)=C2OC)C1=O MAZMPXLFEOXKPB-UHFFFAOYSA-N 0.000 description 1
- AORIDMPHRQRINB-UHFFFAOYSA-N CN1CN(C(O)=O)C2=CC=CC=C2C1=O Chemical compound CN1CN(C(O)=O)C2=CC=CC=C2C1=O AORIDMPHRQRINB-UHFFFAOYSA-N 0.000 description 1
- BKWOKYZSNXYNQD-UHFFFAOYSA-N COC=1C=C2C(N(CN(C2=CC1OC)C(=O)O)C)=O Chemical compound COC=1C=C2C(N(CN(C2=CC1OC)C(=O)O)C)=O BKWOKYZSNXYNQD-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical compound C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QQFHCCQSCQBKBG-UHFFFAOYSA-N methyl 2-amino-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1N QQFHCCQSCQBKBG-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2640670A | 1970-04-07 | 1970-04-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2116079A1 DE2116079A1 (de) | 1972-02-17 |
| DE2116079B2 DE2116079B2 (de) | 1974-06-12 |
| DE2116079C3 true DE2116079C3 (de) | 1975-02-20 |
Family
ID=21831651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712116079 Expired DE2116079C3 (de) | 1970-04-07 | 1971-04-02 | 6,7-Dimethoxy-chinazoline |
Country Status (10)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59175170U (ja) * | 1983-05-09 | 1984-11-22 | 日本碍子株式会社 | 加熱器付酸素濃度検出器 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092631A (en) * | 1963-06-04 | Y-chloro-z-lower alkyl-i | ||
| CH474525A (fr) * | 1967-06-20 | 1969-06-30 | S Chimiques Et Pharma Seceph S | Procédé de préparation de nouveaux dérivés de la quinazoline |
-
1970
- 1970-07-29 GB GB3680870A patent/GB1273916A/en not_active Expired
-
1971
- 1971-04-02 DE DE19712116079 patent/DE2116079C3/de not_active Expired
- 1971-04-05 ES ES389924A patent/ES389924A1/es not_active Expired
- 1971-04-05 CH CH488871A patent/CH522654A/fr not_active IP Right Cessation
- 1971-04-06 NL NL7104580A patent/NL141872B/xx not_active IP Right Cessation
- 1971-04-06 BE BE765343A patent/BE765343A/xx unknown
- 1971-04-07 SE SE460571A patent/SE378595B/xx unknown
- 1971-04-07 FR FR7112339A patent/FR2092015B1/fr not_active Expired
- 1971-04-07 JP JP46021118A patent/JPS502992B1/ja active Pending
-
1974
- 1974-12-30 MY MY7400194A patent/MY7400194A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2116079A1 (de) | 1972-02-17 |
| JPS502992B1 (enrdf_load_stackoverflow) | 1975-01-30 |
| GB1273916A (en) | 1972-05-10 |
| CH522654A (fr) | 1972-06-30 |
| BE765343A (fr) | 1971-10-06 |
| NL141872B (nl) | 1974-04-16 |
| FR2092015B1 (enrdf_load_stackoverflow) | 1975-01-17 |
| NL7104580A (enrdf_load_stackoverflow) | 1971-10-11 |
| FR2092015A1 (enrdf_load_stackoverflow) | 1972-01-21 |
| MY7400194A (en) | 1974-12-31 |
| SE378595B (enrdf_load_stackoverflow) | 1975-09-08 |
| DE2116079B2 (de) | 1974-06-12 |
| ES389924A1 (es) | 1973-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3718450A1 (de) | Biphenyl-hydroxamsaeure-derivate | |
| CH637646A5 (de) | Analgetisch wirksame triazindione, herstellungsverfahren und pharmazeutische zusammensetzungen. | |
| DE2116079C3 (de) | 6,7-Dimethoxy-chinazoline | |
| DE2463023C2 (de) | S-Triazolo-[5,1-a]-isochinolinderivate, deren Salze und Verfahren zu deren Herstellung | |
| DE69614553T2 (de) | Aromatische carbonsaürediamide mit antigastrin wirkung, ihre herstellung und pharmazeutische verwendung | |
| DE3642497A1 (de) | Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte | |
| CH642365A5 (de) | Verfahren zur herstellung von 6-piperidino-2,4-diaminopyrimidin-3-oxid. | |
| DE1468466A1 (de) | Verfahren zur Herstellung substituierter cyclischer Carboxamidoverbindungen | |
| DE2155406C3 (de) | 3- eckige Klammer auf 2-(3-Bromphenyl)-5-tetrazolyl eckige Klammer zu -propionsäureamide | |
| DE1668550C (enrdf_load_stackoverflow) | ||
| CH513848A (de) | Verfahren zur Herstellung von Pyrrolinverbindungen | |
| DE3112164A1 (de) | Benzisothiazolyloxamate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel | |
| DE1645901C3 (de) | gamma-(4-Alkylp!peridino)-p-fluorbutyrophenone und Verfahren zu ihrer Herstellung | |
| DE1543718C3 (de) | Aminoacetomtrilderivate und Ver fahren zu ihrer Herstellung | |
| DE1770669C3 (de) | 1 -Acyl-4-oxo-i ,2,3,4-tetrahydrochinazoline und Verfahren zu ihrer Herstellung | |
| AT365557B (de) | Verfahren zur herstellung von neuen substituierten 7-sec. amino-5,6,8,9-tetrahydro-7h-benzocyclohep-tenen und ihren saeureadditionssalzen | |
| AT346828B (de) | Verfahren zur herstellung von neuen benzhydrylsulfinylalkylamidinen | |
| DE2541434A1 (de) | 5-endo-(3-indolcarbonyloxy)-n- eckige klammer auf amino(niedrig)alkyl eckige klammer zu bicyclo eckige klammer auf 2.2.1 eckige klammer zu -heptan-2,3-di- endo-carbonsaeureimide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE1445469C (de) | 1 - Amino^-hydroxy^-phenyl-piperidinderivate, ihre Säureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE1470284C (de) | beta- geschweifte Klammer auf 1-Methyl-4- eckige Klammer auf l-methyl-4-(l-methyl-4-fonnylamino-pyrrol-2-carboxamido)-pyrrol-2-carboxamido eckige Klammer zu -pyrrol-2carboxamido geschweifte Klammer zu -propionamidin sowie dessen Säureadditionssalze | |
| DE2322070A1 (de) | Neue piperazinderivate | |
| DE1470290A1 (de) | Verfahren zur Herstellung neuer 1-substituierter Cycloheptimidazol-2-(1H)-on-Verbindungen | |
| DE2814798A1 (de) | 4-(2-thienylmethylamino)-benzoesaeure- verbindungen | |
| DE1032257B (de) | Verfahren zur Herstellung neuer Hydantoine | |
| DE2405778A1 (de) | N-mono-(alkoxymethyl)-phenobarbitale, verfahren zu ihrer herstellung und therapeutische massen, die diese verbindungen enthalten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |